Isopropanol → Nilvadipine

HRID 1721024

반응식

HRID 1721024 반응식
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]([C:10]1[CH:11]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:12]([C:19]([O:21][CH3:22])=[O:20])=[C:13]([C:17]#[N:18])[NH:14][C:15]=1[CH3:16])([OH:9])=[O:8].[CH:32](O)([CH3:34])[CH3:33].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[C:17]([C:13]1[NH:14][C:15]([CH3:16])=[C:10]([C:7]([O:9][CH:32]([CH3:34])[CH3:33])=[O:8])[CH:11]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:12]=1[C:19]([O:21][CH3:22])=[O:20])#[N:18]

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 24819Phosphorus pentachlorideHCID 153887666-Cyano-5-methoxycarbonyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

생성물 1

HCID 4494Nilvadipine수율 95.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Phosphorus pentachloride (2.46 g) was added to a suspension of (+)-methyl 5-carboxy-2-cyano-6-methyl-4-(3-nitrophenyl) -1,4-dihydropyridine-3-carboxylate (3.12 g) in methylene chloride (30 ml) under ice-cooling, and the mixture was stirred for 30 minutes. Then, a solution of isopropyl alcohol (1.4 g) in methylene chloride (10 ml) was added dropwise thereto over a period of 10 minutes. After being stirred for 20 minutes, 5% aqueous sodium carbonate (30 ml ) was added to the reaction solution and then stirred at ambient temperature for an hour. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (75 g) using a mixture of benzene and ethyl acetate (10:1) as an eluent. The eluate was evaporated in vacuo and the residue was crystallized from diisopropyl ether to give (+)-5-isopropyl 3-methyl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (3.34 g).

후처리

  1. temperaturecooling
  2. waitover a period of 10 minutes
  3. stirringAfter being stirred for 20 minutes
  4. stirringstirred at ambient temperature for an hour
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with methylene chloride
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (75 g)
  11. additiona mixture of benzene and ethyl acetate (10:1) as an eluent
  12. customThe eluate was evaporated in vacuo
  13. customthe residue was crystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-8ee56fc9a443406c9f89fe63cd33a383
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05508413

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